Stadium: Pista 2 Round: 27 Ground: Clay
| Challenger Barcelona | 2021/10/07 09:00 | Nuno Borges v Teymuraz Gabashvili | 6-7,5-7 |
| Challenger Barcelona | 2021/10/05 13:35 | Nikolas Sanchez Izquierdo v Teymuraz Gabashvili | 5-7,2-6 |
| Challenger - Orleans | 2021/09/26 13:35 | Teymuraz Gabashvili v Titouan Droguet | 2-6,6-3,3-6 |
| Challenger Bukarest | 2021/09/23 11:30 | Teymuraz Gabashvili v Nicholas David Ionel | 3-6,3-6 |
| Challenger Bukarest | 2021/09/21 13:10 | Zdenek Kolar v Teymuraz Gabashvili | 5-7,4-6 |
| Challenger - Rennes | 2021/09/17 12:25 | Teymuraz Gabashvili v Mats Moraing | 2-6,6-7 |
| Challenger - Rennes | 2021/09/16 08:00 | Teymuraz Gabashvili v Ernesto Escobedo | 4-6,6-2,6-3 |
| Challenger - Rennes | 2021/09/14 18:55 | Gilles Simon v Teymuraz Gabashvili | 3-6,2-6 |
| Challenger Barcelona | 2021/10/07 09:00 | Dimitar Kuzmanov v Damir Dzumhur | 6-4,6-4 |
| Challenger Barcelona | 2021/10/05 13:10 | Dimitar Kuzmanov v Tommy Robredo | 6-0,6-1 |
| ATP Sofia | 2021/09/29 16:55 | Kamil Majchrzak v Dimitar Kuzmanov | 7-5,6-1 |
| ATP Sofia | 2021/09/28 15:10 | Dimitar Kuzmanov v Lorenzo Musetti | 6-7,7-6,6-3 |
| Challenger Biel | 2021/09/20 12:45 | Tobias Kamke v Dimitar Kuzmanov | 6-4,7-6 |
| Challenger - Banja Luka | 2021/09/08 10:50 | Dimitar Kuzmanov v Zdenek Kolar | 5-7,2-6 |
| Challenger - Banja Luka | 2021/09/06 14:10 | Dimitar Kuzmanov v Alexander Shevchenko | 3-6,6-4,6-1 |
| Challenger Mallorca | 2021/09/02 17:00 | Dimitar Kuzmanov v Lukas Lacko | 2-6,6-7 |